Check for updates before you fly
The Trump presidency has so far been characterized by rapid legal changes and a general sense of unpredictability. With that in mind, it’s best to check for the latest updates just before you fly.
Make sure your trip fits into one of the accepted categories
There are 12 visa categories that allow US travellers to visit Cuba. They include family visits, “support for the Cuban people,” and religious activities. It’s most likely that you will be accepted under “support for the Cuban people” if you can prove that you plan to stay in casas particulares run by local people.
Avoid government-run establishments
One of the main aims of Trump’s new rules is to stop tourism from benefiting the Cuban regime, and most of all the military. There is a list of establishments that US travellers are banned from visiting, including some of the major hotel chains on the island, due to links to the military.
Fly via Mexico or another country
If you don’t want to worry about visa categories or other restrictions, you can do what adventurous US travellers have been doing for years. Simply book a flight to Mexico or Canada and fly from there to Cuba. No one will ask you any questions in Cuba.
Don’t listen to everything you hear
To listen to certain media outlets in the US, you would think that Cuba was a terrible place filled with danger. In fact the opposite is true. Americans are well received on the island, and crime rates are low compared to other countries in Latin America.
Take out cash before you travel
While other nationalities can make use of a growing network of ATMs, it’s important to remember that the same is not possible with US bank cards. You’ll have to take out as much cash as you need for your trip before you travel.
Plan your trip for the best weather
Visit between mid-November and March to enjoy the coolest and driest part of the year, which is also the busiest period. You can avoid the crowds by traveling in May and June, but it’s the rainy season. July to November is to be avoided because it’s hurricane season, but you could still book last minute trips if the forecast looks good.